Nonaqueous electrolytes for electrochemical cells

Abstract

A compound of formula (I) [Formula 1] TIFF2025510827000018.tif45143Core is a core group, X is Al or B, and R 1 is, independently in each occurrence, a substituent, and two R 1 The groups can be linked to form a ring, L is a linking group, and M + is a cation and n is at least 2. The compound may be used in a battery, for example a metal battery.

Description

[Background technology]

[0001] US2019 / 0185492 discloses ionic covalent frameworks containing four-coordinate borate bonds.

[0002] Aubrey et al, “Dependence of Linker Length and Composition on Ionic Conductivity and Lithium Deposition in Single-Ion Conducting Network Polymers”, Macromolecules 2021 54(16), 7582-7589 disclose polymers containing borate groups linked by oligoethyleneglycoxide linkers.

[0003] JPH08301879 discloses compounds of formulae (II) and (III). [ka] Summary of the Invention

[0004] In some embodiments, the disclosure provides a compound of formula (I): [ka] During the ceremony, Core is a core group; X is Al or B; R 1 is, independently in each occurrence, a substituent, and two R 1 the groups may be linked to form a ring, L is a linking group; M + is a cation, n is at least 2.

[0005] In some embodiments, R 1In these embodiments, each R 1 is independently 1~20 It is an alkyl group, in which one or more non-adjacent C atoms of the alkyl group can be replaced by O, S, CO, or COO, and one or more H atoms of the alkyl group can be replaced by F.

[0006] Optionally, each R 1 are independently selected from alkyl groups and alkyl ether groups, and one or more H atoms may be replaced with F.

[0007] Optionally, each R 1 is the same.

[0008] Optionally, the compound comprises at least two different R 1 Contains a group.

[0009] In some embodiments, two R 1 groups are linked so that the compound of formula (I) has the formula (Ia): [ka] In the formula, R 2 is, in each occurrence, independently a divalent organic group.

[0010] Optionally, L is O.

[0011] Optionally, n is 2, 3, or 4.

[0012] Optionally, the core comprises: -(Ar 2 )p (p is at least 1, preferably 1, 2, or 3; Ar 2 is, at each occurrence, independently an arylene or heteroarylene group that is unsubstituted or substituted with one or more substituents; -N(R 8 )x(R 9 )y(R 8 is a divalent organic group, R 9is a monovalent group, x is 2 or 3, and y is 3-x; and -Ak (Ak is a linear or branched C 1~20 alkylene, wherein one or more non-adjacent C atoms may be replaced by O, S, CO, or COO, and one or more C atoms may be replaced by arylene or heteroarylene.

[0013] Optionally, M + is an alkali metal ion, preferably a lithium ion.

[0014] Optionally, M + is a solvated cation.

[0015] Optionally, the solvate of the solvent is selected from a solvent containing at least one ether group.

[0016] Optionally, the solvate: M + The molar ratio of does not exceed 10:1.

[0017] Optionally, the solvate: M + is at least 0.5:1.

[0018] In some embodiments, the disclosure provides a formulation comprising a compound of formula (I) and a solvent. Optionally, the formulation also comprises a solvate: M + The molar ratio of does not exceed 20:1.

[0019] In some embodiments, the disclosure provides a method of forming a compound described herein, comprising reacting a compound of formula (II) and a compound of both formulas (III) and (IV). [ka]

[0020] Optionally, the reaction is carried out in a reaction mixture that includes a solvent for the solvates mentioned above.

[0021] Optionally, the method includes at least partially replacing the solvent of the solvate of the compound with another solvent.

[0022] In some embodiments, the present disclosure provides a metal or metal-ion battery comprising a negative electrode, a positive electrode, and a compound described herein disposed between the negative electrode and the positive electrode.

[0023] Optionally, the solvate of the battery: M + The molar ratio of does not exceed 10:1.

[0024] Optionally, the metal battery includes an anode protection layer comprising a compound or polymer disposed between the anode and cathode. [Brief description of the drawings]

[0025] [Figure 1] FIG. 1 is a schematic diagram of a battery according to some embodiments of the present disclosure having a separator comprising a compound described herein. [Diagram 2] FIG. 1 is a schematic diagram of a battery according to some embodiments of the present disclosure having an anode protective layer comprising a compound described herein. [Diagram 3] 1 is an NMR spectrum of a compound according to one embodiment of the present disclosure. [Figure 4] 1 shows Nyquist plots for a cell according to an embodiment of the present disclosure and a comparative cell. [Diagram 5] 4 shows the current profile applied to the tested cell. [Figure 6A] FIG. 1 shows EIS measurements (left) for a cell according to one embodiment of the present disclosure. [Figure 6B] 1 shows DC measurements on a cell according to one embodiment of the present disclosure. [Figure 7A] EIS measurements (left) are shown for a comparison cell. [Figure 7B] DC measurements are shown for a comparison cell.

[0026] The drawings are not drawn to scale and have various perspectives and viewing angles. The drawings are of several implementations and examples. While the technology is susceptible to various modifications and alternative forms, specific embodiments are shown by way of example in the drawings and are described in detail below. However, it is not intended to limit the technology to the specific implementations described. On the contrary, the technology is intended to cover all modifications, equivalents, and alternatives falling within the scope of the technology as defined by the appended claims. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0027] Unless the context clearly requires otherwise, throughout the specification and claims, words such as "comprise," "comprising," and the like shall be interpreted in an inclusive sense, i.e., "including but not limited to," as opposed to an exclusive or exhaustive sense. Additionally, the words "herein," "on," "under," and words of similar meaning, when used in this application, refer to this application as a whole and not to any particular portion of this application. Where the context permits, words in the Detailed Description using the singular or plural may also include the plural or singular, respectively. The word "or" in connection with a list of two or more items encompasses all of the following interpretations of that word: any of the items in the list, all of the items in the list, and any combination of the items in the list. As used in this application, a reference to a layer "over" another layer means that the layers may be in direct contact or that there may be one or more intervening layers. As used in this application, a reference to a layer "on" another layer means that the layers are in direct contact. A reference to an element of the periodic table includes any isotopes of that element.

[0028] The teachings of the technology provided herein may be applied to other systems, not necessarily the systems described below. Elements and acts of the various examples described below can be combined to provide further implementations of the technology. Some alternative implementations of the technology may include additional elements to those implementations described below, as well as fewer elements.

[0029] These and other changes may be made to the technology in light of the detailed description below. Although the description describes certain examples of the technology and describes the best mode contemplated, no matter how detailed the description may appear, the technology may be implemented in many ways. As described above, a particular term used when describing a particular feature or aspect of the technology should not be interpreted as meaning that the term is redefined herein to be limited to any particular feature, characteristic, or aspect of the technology associated with that term. In general, the terms used in the following claims should not be interpreted as limiting the technology to the particular embodiments disclosed herein, unless such terms are otherwise expressly defined in the Detailed Description section. Thus, the actual scope of the technology encompasses not only the disclosed embodiments, but all equivalent ways of implementing or performing the technology according to the claims.

[0030] In order to reduce the number of claims, certain aspects of the technology are presented below in certain claim forms, but applicants contemplate various aspects of the technology in any number of claim forms.

[0031] In the following description, for purposes of explanation, numerous specific details are set forth in order to provide a thorough understanding of the implementation of the disclosed technology. However, it will be apparent to one skilled in the art that embodiments of the disclosed technology may be practiced without some of these specific details.

[0032] In some embodiments, the disclosure provides a compound of formula (I): [ka]

[0033] X is Al or B.

[0034] R 1 is, independently in each occurrence, a substituent, and two R 1 The groups may be linked to form a ring.

[0035] M + is a cation.

[0036] L is a linking group, optionally O, S, or NR 4 and R 4 is H or a substituent.

[0037] The core is a core unit to which n aluminate or borate groups are attached.

[0038] n is at least 2, optionally 2 to 6, preferably 2, 3, or 4.

[0039] Preferably, L is O.

[0040] L is NR 4 If R 4 is preferably H, optionally substituted aryl, optionally substituted heteroaryl, and C 1~12 alkyl, C 1~12 One or more non-adjacent, non-terminal C atoms of an alkyl are O, S, CO, COO, or NR 5 can be replaced by C 1~12 One or more H atoms of the alkyl may be replaced by F, R 5 is H or a substituent, preferably H or C 1~6 It is an alkyl.

[0041] an aryl or heteroaryl group R 4 is preferably phenyl. When present, the aryl or heteroaryl group R 4The substituents are preferably F, CN, NO 2、 and C 1~12 alkyl, C 1~12 One or more non-adjacent, non-terminal C atoms of an alkyl may be O, S, NR 5 , CO, or COO, and one or more H atoms may be replaced by F.

[0042] Preferably, the core group is -(Ar 2 )p (p is at least 1, preferably 1, 2, or 3; Ar 2 is, at each occurrence, independently an arylene or heteroarylene group that is unsubstituted or substituted with one or more substituents; -N(R 8 )x(R 9 )y(R 8 is a divalent organic group, R 9 is a monovalent group, x is 2 or 3, and y is 3-x; and -Ak (Ak is a linear or branched C 1~20 alkylene, where one or more non-adjacent C atoms may be replaced by O, S, CO, or COO, and one or more C atoms may be replaced by arylene or heteroarylene, preferably phenylene.

[0043] Ar 2 is preferably, in each occurrence, C 6~10 arylene, or a 5- or 6-membered heteroarylene ring.

[0044] Formula (Ar 2 Exemplary core groups for p include benzene, biphenylene, and pyridine, each of which can be unsubstituted or substituted with one or more non-ionic substituents.

[0045] Ar 2 Exemplary non-ionic substituents of are F, CN, NO, N(R 10 )2, and R 10is, at each occurrence, independently, H or aryl, preferably phenyl, and C 1~12 alkyl, with one or more non-adjacent, non-terminal C atoms being O, S, NR 7 , CO, or COO, and one or more H atoms may be replaced by F.

[0046] R 7 is H or a substituent, preferably R 4 The compound is selected from the groups defined for

[0047] The formula N(R 8 )x(R 9 ) for the y core group, each R 8 is preferably an optionally substituted arylene, preferably benzene, an optionally substituted heteroarylene, and C 1~12 alkylene, one or more non-adjacent C atoms may be replaced by O, S, CO, COO, or arylene, and one or more H atoms may be replaced by F.

[0048] If y is 1, then R 9 is preferably optionally substituted aryl, preferably benzene, optionally substituted heteroaryl, and C 1~12 alkylene, wherein one or more non-adjacent C atoms are O, S, CO, COO, NR 5 or arylene, and one or more H atoms may be replaced by F.

[0049] R 8 or R 9 Exemplary substituents for the aryl(ene) or heteroaryl(ene) groups are F, CN, NO, and C 1~12 alkyl, where one or more non-adjacent C atoms are O, S, CO, COO, or NR 5 can be replaced by

[0050] The formula N(R 8 )x(R 9 Exemplary core groups for y include tri(C1~12 ) alkylamine, where at least two of the three alkyl groups are attached to the L group of formula (I).

[0051] Exemplary core groups A include 2-methylpropane bonded to two or three L groups, tert-butane bonded to two or three L groups, neopentane bonded to two, three or four L groups, and a group of formula C(CH2CH2OCH2CH2-)4 bonded to four L groups. Halogenated, more preferably fluorinated, core groups A are preferred.

[0052] As used herein, the "terminal C atom" of an alkyl group means the C atom of a methyl group at the chain end of a straight-chain or branched alkyl group, respectively.

[0053] The core is non-polymeric. As used herein, "non-polymeric" means that the core is not polydisperse. Preferably, the core has a molecular weight not exceeding 800 Daltons.

[0054] In some preferred embodiments, R 1 None of the groups are linked. Optionally according to these embodiments, each R 1 is independently 1~20 It is an alkyl group, in which one or more non-adjacent C atoms of the alkyl group can be replaced by O, S, CO, or COO, and one or more H atoms of the alkyl group can be replaced by F.

[0055] Preferred R 1 The group is C 1~20 Contains alkyl, OR 1 One or more C atoms other than the C atom bonded to O or a terminal C atom may be replaced by O, and one or more H atoms may be replaced by F.

[0056] In some embodiments, each R 1 is the same.

[0057] In some embodiments, the compound has two or more different R1 Contains a group.

[0058] In some embodiments, two R 1 groups are linked so that the compound of formula (I) has the formula (Ia): [ka] In the formula, R 2 is, independently in each occurrence, a divalent group; R 3 is a trivalent organic group.

[0059] Optionally, R 2 is C 6~20 Optionally, the substituents are selected from arylene groups, such as 1,2-phenylene, which may be unsubstituted or substituted with one or more substituents; biarylene groups, such as 2,2'-linked biphenylene; ethylene; propylene; and diethyleneamine, each of which may be unsubstituted or substituted with one or more substituents. Optionally, the substituents are selected from F alkyl, C 1~12 One or more non-terminal C atoms of the alkyl may be replaced by F, 1~12 One or more C atoms of an alkyl may be replaced by O.

[0060] Optionally, R 3 is a trivalent amine, e.g., triethyleneamine, a trivalent group -(Ar 2 ) p or a trivalent group Ak.

[0061] Preferably, M + is an alkali metal cation, more preferably a lithium cation.

[0062] Preferably, M + is a solvated cation.

[0063] Preferably, the solvent of the solvate is selected from solvents containing at least one ether group.

[0064] Preferably, the solvent contains two or more groups capable of coordinating to a metal cation.

[0065] The solvents include linear and cyclic compounds containing one or more ether groups and, optionally, one or more groups selected from hydroxyl groups and carboxylate groups; and solvents containing carbonate groups, e.g., C 2~10 Alkylene carbonate and di(C 1~10 The alkyl carbonate may be selected from the group consisting of aryl, aryl, aryl and alkyl carbonates.

[0066] Exemplary solvents include, but are not limited to, polypropylene carbonate, ethylene carbonate, dimethyl carbonate, tetrahydrofuran, dimethoxyethane (DME), diglyme (diethylene glycol dimethyl ether), triglyme (triethylene glycol dimethyl ether), tetraglyme (tetraethylene glycol dimethyl ether), and crown ethers, such as 12-crown-4 and 1-aza-12-crown-4.

[0067] The compounds may contain solvents of multiple solvation.

[0068] Optionally, the battery containing the compound of formula (I) does not contain any solvent or only a small amount of solvent, preferably M + The presence of small amounts of solvent has been found to greatly increase the ionic conductivity of compounds of formula (I). This increase is due to solvation of the cations, and when solvation occurs, M + It will be understood that the is solvated by at least some, but not necessarily all, of the solvent present. The presence of small amounts of organic solvents, such as ether- or carbonate-containing solvents, may enhance ionic conductivity while significantly reducing flammability compared to ionic compounds dissolved in larger amounts of such solvents. In some embodiments, all solvents are solvating solvents only. In some embodiments, there is a solvating solvent and an additional free (non-solvating) solvent.

[0069] Thus, the formulation comprising the solvent and the compound of formula (I) preferably comprises M + Preferably, the formulation comprises not more than 20 moles of solvent, optionally not more than 10 moles, or not more than 8 or 6 moles of solvent per mole of M + At least 0.5 mole or at least 1 mole of solvent per mole of

[0070] The amount of solvating solvent in the compound of formula (I) corresponds to the solvent 1 H NMR peaks and -OR 1 The integration of the peaks corresponding to the groups gives the compound after vacuum treatment to remove the free (non-solvated) solvent. 1 It can be determined from the 1 H NMR spectrum.

[0071] A compound of formula (I) may be formed by reacting a compound of formula (II) and both compounds of formulas (III) and (IV). [ka]

[0072] Exemplary compounds of formula (I) include, but are not limited to, lithium aluminum hydride (LiAlH4), lithium borohydride (LiBH4).

[0073] Metal cation M + When is a solvated cation, in some embodiments, a solvent for the solvate is present in the reaction mixture containing the compound of Formula (II) and the compound of Formula (III).

[0074] In some embodiments, the solvent of a compound of formula (I) containing a solvated cation may be replaced with a different solvent. Methods of changing the solvent of a solvate include, but are not limited to, removing the solvent of the compound of formula (I) by heat treatment and replacing it with another solvent that can solvate the cation, and contacting the compound of formula (I) with a solvent that coordinates more strongly to the cation than the existing solvation solvent, for example by treating a compound of formula (I) having a monodentate solvation solvent with a bidentate or tridentate or higher ligand.

[0075] Purpose The single-ion conducting compound of formula (I) described herein may be provided in a rechargeable battery cell. The battery may be, but is not limited to, a metal battery or a metal ion battery, such as a lithium battery or a lithium ion battery.

[0076] The compound of formula (I) may be a component of a composite material that includes one or more additional materials, such as one or more polymers. A composition that includes a compound of formula (I) and a polymer may form a gel.

[0077] A layer comprising or consisting of a compound of formula (I) may be formed by depositing a formulation containing the material dissolved or dispersed in a solvent or solvent mixture. Optionally, a battery comprising a compound of formula (I) may be formed by depositing a formulation containing the material dissolved or dispersed in a solvent or solvent mixture. + Not more than 20 moles of solvent per mole of M + and / or contains no more than 10 moles of solvent per mole of solvent and / or contains no solvent other than any solvating solvents described herein.

[0078] The formulation may include a polymeric additional material dissolved in a solvent.

[0079] FIG. 1 shows a battery including an anode current collector 101 carrying an anode 103 thereon, a cathode current collector 109 having a cathode 107 disposed thereon, and a separator 105 disposed between the anode and cathode. The separator comprises or consists of a compound of formula (I). Preferably, the separator is a compound of formula (I)+ and / or does not contain more than 10 moles of solvent per mole of solvent other than any solvating solvents described herein.

[0080] The battery may be a metal battery.The battery may be a metal ion battery.

[0081] In a metal battery, the negative electrode is a layer of metal (eg, lithium) that forms on the negative electrode current collector during charging of the battery and is removed during discharging of the battery.

[0082] In the case of metal ion batteries, the negative electrode comprises an active material for absorbing metal ions, such as graphite.

[0083] The positive electrode may be selected from any positive electrode known to one of skill in the art.

[0084] The negative and positive current collectors can be any suitable conductive material known to those skilled in the art, for example, one or more layers of a metal or metal alloy, such as aluminum or copper.

[0085] 1 shows a battery in which the negative and positive electrodes are separated only by a separator. In other embodiments, one or more additional layers may be disposed between the negative electrode and the separator and / or between the positive electrode and the separator.

[0086] FIG. 2 shows a battery, preferably a metal battery, including an anode current collector 101 carrying an anode 103 on its surface, a cathode current collector 109 having a cathode 107 disposed on its surface, a separator 105 disposed between the anode and the cathode, and an anode protective layer 111 disposed between the anode and the separator. The separator may include or consist of a compound described herein or any other separator known to those skilled in the art, such as a porous polymer in which a liquid electrolyte is absorbed. The anode protective layer includes or consists of a compound of formula (I) described herein. The anode protective layer may prevent or delay the formation of lithium metal dendrites in a metal battery. EXAMPLES

[0087] Compound Example 1 Compound Example 1 was prepared according to the following reaction scheme. [ka]

[0088] To a solution of lithium aluminum hydride (9 ml, 9.0 mmol, 1.0 M in tetrahydrofuran) was added dropwise a solution of 2,2,3,3,4,4,5,5-octafluoro-1-pentanol (3.74 ml, 27.0 ml) in anhydrous 1,2-dimethoxyethane (5 ml) at room temperature. The resulting solution was stirred for 30 minutes. 1,3,5-trihydroxybenzene (0.377 g, 3.0 mmol) was dissolved in 1,2-dimethoxyethane (5 ml) and added to the stirred reaction mixture at room temperature. The reaction mixture was stirred at room temperature for 1 hour, and then it was heated to 60° C. for 2 hours. The mixture was cooled to room temperature and left under nitrogen overnight. An additional solution of lithium aluminum hydride (0.4 ml, 0.4 mmol, 1.0 M in tetrahydrofuran) was added to the reaction mixture at room temperature, and the mixture was heated to 60° C. for 2 hours, and then cooled to room temperature.

[0089] Remove excess solvent by reducing pressure (3.0×10 -2 The mixture was removed under 1000 mbar at room temperature to give a thick, opaque oil.

[0090] Referring to Figure 3, the NMR spectrum of the product shows the presence of a mixture of compounds in the product. From the integration of the NMR peaks, it was calculated that for every three molecules of 2,2,3,3,4,4,5,5-octafluoro-1-pentanol in the product mixture, there are 2.0 molecules of 1,2-dimethoxyethane and 0.75 molecules of tetrahydrofuran as residual solvents that are believed to solvate the lithium ion of compound Example 1.

[0091] Cell Example 1 EIS measurements were performed in a 2032-type coin cell device (casing purchased from Cambridge Energy Solutions) with the following layers placed, in order, between the bottom and top of the coin cell: Stainless Steel Disc Lithium Disk A fluorosilicone stencil (purchased from Silex Silicones) shaped as a 15.5 mm diameter disk with a 5 mm diameter circular hole cut in the center. 30 microliters of electrolyte of compound Example 1 filled into the circular hole; Lithium Disk Stainless Steel Disc Wave spring.

[0092] The coin cells were crimped to give a cell with a stencil thickness of 360 microns.

[0093] The electrolyte was Compound Example 1, DME(Li + 2.05 moles per mole of Li + The mixture consisted of 0.18 moles per mole of .

[0094] Comparison cell 1 A cell was prepared as described for Cell Example 1, except that compound LiAl(OFP)4 was used instead of compound Example 1. [ka]

[0095] LiAl(OFP)4 contained 0.85 molecules of DME and 1.13 molecules of propylene carbonate per lithium cation.

[0096] Electrochemical Impedance Spectroscopy (EIS) EIS measurements on the coin cells were performed at room temperature over a frequency range of 1 Hz to 1 MHz with an amplitude of 5 mV using a potentiostat (Interface 1010E, Gamry Instruments).

[0097] The ionic conductivity was calculated using the following formula:

number

[0098] The impedance of the cell was determined by determining the intercept of the first semicircle on the x-axis of the Nyquist plot.

[0099] The Nyquist plots for Cell Example 1 and Comparative Cell 1 are shown in Figure 4. As shown in Table 1, the ionic conductivities for the two compounds are of the same order of magnitude. [Table 1]

[0100] Lithium transport number (LTN) LTN measurements were performed in the cell described herein using the Evans method described in J. Evans et al., Polymer, 1987, Vol 28.

[0101] Prior to LTN measurements, the devices were subjected to lithium plating and stripping cycles in a battery test system (Arbin Instruments) for 18 h at 1 μA / cm 2 The animals were preconditioned by applying

[0102] A constant current (negative or positive) was applied for 60 minutes with a 30 minute rest period between plating and stripping intervals according to the profile shown in FIG.

[0103] After preconditioning, measurements to determine LTN were performed as follows. 1. A first EIS spectrum was taken. 2. This was followed by DC current measurements (at a constant voltage of 10 mV applied for 120 min) on a battery test system (Arbin Instruments). 3. This was followed by a second EIS measurement.

[0104] EIS measurements were carried out as described above.

[0105] LTN was calculated according to the following formula, based on the model developed by Evans et al. (ibid.):

number

[0106] The parameters extracted from these plots are summarized in Table 2, together with the calculated LTN values ​​for compound Example 1 and LiAl(OFP)4, which show a higher LTN for compound Example 1. [Table 2]

Claims

1. A compound of formula (I) 【Chemistry 1】 During the ceremony, the core is a core group; X is Al or B; R １ is, independently in each occurrence, a substituent; １ the groups may be linked to form a ring, L is a linking group; M ＋ is a cation, A compound wherein n is at least 2.

2. The R １ The compound of claim 1 , wherein none of the groups are linked.

3. Each R １ But independently, C １～２０ The compound according to claim 2, wherein the alkyl group is an alkyl group, one or more non-adjacent C atoms of which may be replaced by O, S, CO, or COO, and one or more H atoms of which may be replaced by F.

4. Each R １ are independently selected from alkyl and alkyl ether groups, and one or more H atoms may be replaced with F.

5. Each R １ The compound according to any one of claims 2 to 4, wherein are the same.

6. The compound has at least two different R １ The compound according to any one of claims 1 to 4, which contains a group.

7. The two R １ groups are linked and the compound of formula (I) has the formula (Ia): 【Chemistry 2】 In the formula, R ２ The compound of claim 1 , wherein, at each occurrence, is independently a divalent organic group.

8. 2. A compound according to any one of the preceding claims, wherein L is O.

9. 2. A compound according to any one of the preceding claims, wherein n is 2, 3 or 4.

10. The core, - (Ar ２ ) p (p is at least 1, preferably 1, 2, or 3; Ar ２ is, at each occurrence, independently an arylene or heteroarylene group that is unsubstituted or substituted with one or more substituents; -N(R ８ ) x (R ９ ) y(R ８ is a divalent organic group, R ９ is a monovalent group, x is 2 or 3, and y is 3-x; and -Ak (Ak is a linear or branched C １～２０ The compound according to any one of the preceding claims, wherein the alkylene is selected from the group consisting of: alkylene, wherein one or more non-adjacent C atoms may be replaced by O, S, CO or COO, and wherein one or more C atoms may be replaced by arylene or heteroarylene.

11. M ＋ 4. A compound according to any one of the preceding claims, wherein is an alkali metal ion.

12. M ＋ The compound of claim 11 , wherein is a lithium ion.

13. M ＋ 4. A compound according to any one of the preceding claims, wherein is a solvated cation.

14. 14. The compound of claim 13, wherein the solvate of the solvent is selected from solvents containing at least one ether group and at least one carbonate group.

15. Solvate: M ＋ 15. The compound according to claim 13 or 14, wherein the molar ratio of does not exceed 10:

1.

16. Solvate: M ＋ The compound according to any one of claims 13 to 15, wherein the molar ratio of is at least 0.5:

1.

17. A formulation comprising a compound according to any one of the preceding claims and a solvent.

18. Solvate: M ＋ 18. The formulation of claim 17, wherein the molar ratio of does not exceed 20:

1.

19. A method of forming a compound according to any one of claims 1 to 16, comprising reacting a compound of formula (II) and a compound of both formulas (III) and 4. 【Chemistry 3】

20. 20. The method of claim 19, wherein the reaction is carried out in a reaction mixture comprising the solvent of the solvate of claim 13 or 14.

21. 17. A method comprising at least partially replacing the solvent of the solvate of the compound of claim 15 or 16 with another solvent.

22. 17. A metal or metal-ion battery comprising a negative electrode, a positive electrode, and a compound according to any one of claims 1 to 16 disposed between said negative electrode and said positive electrode.

23. The battery includes a solvent, and the solvent of the battery: M ＋ 23. The metal or metal-ion battery of claim 22, wherein the molar ratio of does not exceed 20:

1.

24. 24. The metal battery according to claim 22 or 23, comprising an anode protective layer comprising the compound according to any one of claims 1 to 16 disposed between the anode and the cathode.

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